Substituted aryl ketones

ABSTRACT

The invention relates to novel substituted aryl ketones of the general formula (I)  
                 
 
     in which  
     n, A, R 1 , R 2 , R 3 , R 4  and Z are each as defined in the description,  
     to processes for their preparation and to their use as herbicides.

[0001] The invention relates to novel substituted aryl ketones, toprocesses for their preparation and to their use as herbicides.

[0002] It is already known that certain substituted aryl ketones haveherbicidal properties (cf. EP-A-090262, EP-A-135 191, EP-A-186 118,EP-A-186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175,EP-A-487 357, EP-A-527 036, EP-A-527 037; EP-A-560 483, EP-A-609 797,EP-A-609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, U.S. Pat. No.5,804,532, U.S. Pat. No. 5,834,402, U.S. Pat. No. 5,846,906, U.S. Pat.No. 5,863,865, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200,WO-A-96/26206, WO-A-97/27187, WO-A-97/35850, WO-A-97/41105,WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270,WO-A-97/46530, WO-A-98/28981, WO-A 98/31682, WO-A-99/03856,WO-A-99/07688). However, the activity of these compounds is not entirelysatisfactory.

[0003] This invention, accordingly, provides the novel substituted arylketones of the general formula (I)

[0004] in which

[0005] n represents the numbers 0, 1 or 2,

[0006] A represents a single bond or represents alkanediyl,

[0007] R¹ represents hydrogen or represents in each case optionallysubstituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, arylor arylalkyl,

[0008] R² represents hydrogen, amino, or represents in each caseoptionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl,alkenyloxy, alkinyl, alkinyloxy, cycloalkyl, cycloalkylalkyl, aryl,arylamino or arylalkyl,

[0009] R³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl,

[0010] R⁴ represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbonyl, halogen, or represents in each case optionally substitutedalkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and

[0011] Z represents one of the groupings below

[0012] where

[0013] m represents the numbers 0 to 6,

[0014] R⁵ represents halogen or represents in each case optionallysubstituted alkyl or alkylthio, or—if mi represents 2—together with asecond radical R⁵ represents alkanediyl (alkylene),

[0015] R⁶ represents hydroxyl, formyloxy, or represents in each caseoptionally substituted alkoxy, alkylthio, alkylcarbonyloxy,alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy,alkinyloxy, arylalkyl, aryloxy, arylthio, arylcarbonyloxy,arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy or arylalkylthio,

[0016] R⁷ represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,or represents in each case optionally substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl or cycloalkyl,

[0017] R⁸ represents hydrogen or represents in each case optionallysubstituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, arylor arylalkyl,

[0018] R⁹ represents hydroxyl, formyloxy, or represents in each caseoptionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy,arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy,

[0019] R¹⁰ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally substituted alkyl,alkylcarbonyl, alkoxy, alkoxycarbonyl or alkylthio,

[0020] R¹¹ represents hydrogen or represents in each case optionallysubstituted alkyl or cycloalkyl,

[0021] R¹² represents hydrogen or represents in each case optionallysubstituted alkyl or cycloalkyl, and

[0022] R¹³ represents hydrogen, cyano, carbamoyl, halogen, or representsin each case optionally substituted alkyl, alkoxy, alkoxycarbonyl,alkylthio, alkylsulphinyl or alkylsulphonyl,

[0023] including all possible tautomeric forms of the compounds of thegeneral formula (I) and the possible salts of the compounds of thegeneral formula (I).

[0024] In the definitions, the hydrocarbon chains, such as alkyl oralkanediyl, are in each case straight-chain or branched—including incombination with heteroatoms, such as in alkoxy.

[0025] Preferred substituents and preferred ranges of the radicalspresent in the formulae mentioned above and below are defined below.

[0026] A preferably represents a single bond or represents alkanediylhaving 1 to 6 carbon atoms.

[0027] R¹ preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally cyano- or halogen-substituted alkenylor alkinyl having in each case 2 to 6 carbon atoms, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkylor cycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atomsin the alkyl moiety.

[0028] R² preferably represents hydrogen, amino, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy,alkylamino or di-alkylamino having in each case 1 to 6 carbon atoms inthe alkyl groups, represents in each case optionally cyano- orhalogen-substituted alkenyl, alkenyloxy, alkinyl or alkinyloxy having ineach case 2 to 6 carbon atoms, represents in each case optionallycyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl, arylamino or arylalkyl having ineach case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4carbon atoms in the alkyl moiety.

[0029] R³ preferably represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallycyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1to 6 carbon atoms in the alkyl groups.

[0030] R⁴ preferably represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallycyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1to 6 carbon atoms in the alkyl groups.

[0031] m preferably represents the numbers 0, 1, 2, 3 or 4.

[0032] R⁵ preferably represents halogen or represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl oralkylthio having in each case 1 to 6 carbon atoms, or optionally also—ifm represents 2—together with a second radical R⁵ represents alkanediyl(alkylene) having 2 to 6 carbon atoms.

[0033] R⁶ preferably represents hydroxyl, formyloxy, or represents ineach case optionally cyano-, halogen- or C₁-C₄-alkoxy-substitutedalkoxy, alkylthio, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy or alkylsulphonyloxy having in each case 1 to 6carbon atoms in the alkyl groups, represents in each case optionallycyano- or halogen-substituted alkenyloxy or alkinyloxy having in eachcase 2 to 6 carbon atoms, or represents in each case optionally nitro-,cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted arylalkyl, aryloxy, arylthio,arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy orarylalkylthio having in each case 6 or 10 carbon atoms in the aryl groupand optionally 1 to 4 carbon atoms in the alkyl moiety.

[0034] R⁷ preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1to 6 carbon atoms in the alkyl groups, or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms.

[0035] R⁸ preferably represents hydrogen, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl having 1to 6 carbon atoms, represents in each case optionally cyano- orhalogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in eachcase 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4carbon atoms in the alkyl moiety, or represents in each case optionallynitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted aryl or arylalkylhaving in each case 6 or 10 carbon atoms in the aryl group andoptionally 1 to 4 carbon atoms in the alkyl moiety.

[0036] R⁹ preferably represents hydroxyl, formyloxy, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkoxy,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy oralkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkylgroups, represents in each case optionally cyano- or halogen-substitutedalkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, orrepresents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted arylalkoxy, arylcarbonyloxy,arylcarbonylalkoxy or arylsulphonyloxy having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety.

[0037] R¹⁰ preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or C₁-C₄-alkoxy substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl or alkylthio having in each case 1 to 6 carbon atoms inthe alkyl groups.

[0038] R¹¹ preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms orrepresents optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl having 3 to 6 carbon atoms.

[0039] R¹² preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms orrepresents optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl having 3 to 6 carbon atoms.

[0040] R¹³ preferably represents hydrogen, cyano, carbamoyl, halogen, orrepresents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atomsin the alkyl groups.

[0041] A particularly preferably represents a single bond or representsalkanediyl having 1 to 4 carbon atoms.

[0042] R¹ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, di-fluoromethoxy- ortrifluoromethoxy-substituted phenyl, benzyl or phenyl-ethyl.

[0043] R² particularly preferably represents hydrogen, amino, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,ethylamino, n- or i-propylamino, n-, i- or s-butylamino, dimethylaminoor diethylamino, represents in each case optionally cyano-, fluorine-,chlorine- or bromine-substituted propenyl, butenyl, propenyloxy,butenyloxy, propinyl, butinyl, propinyloxy or butinyloxy, represents ineach case optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylamino, benzyl or phenylethyl.

[0044] R³ particularly preferably represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-,s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-,s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonylor diethylaminosulphonyl.

[0045] R⁴ is particularly preferably represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-,s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-,s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonylor diethylaminosulphonyl.

[0046] m particularly preferably represents the numbers 0, 1, 2 or 3.

[0047] R⁵ particularly preferably represents fluorine, chlorine,bromine, or represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-,i-, s- or t-butylthio, or optionally also—if m represents 2—togetherwith a second radical R⁵ represents ethane-1,2-diyl (di-methylene),propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).

[0048] R⁶ particularly preferably represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-,s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy,propinyloxy or butinyloxy, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenoxy, phenylthio, benzoyloxy,benzoylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio orbenzyl.

[0049] R⁷ particularly preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0050] R⁸ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl or benzyl.

[0051] R⁹ particularly preferably represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy,represents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-,s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenylmethoxy, benzoyloxy, benzoylmethoxy or phenylsulphonyloxy.

[0052] R¹⁰ particularly preferably represents hydrogen, cyano,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-,ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio.

[0053] R¹¹ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0054] R¹² particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0055] R¹³ particularly preferably represents hydrogen, cyano,carbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl.

[0056] A very particularly preferably represents a single bond orrepresents methylene (CH₂), dimethylene (ethane-1,2-diyl, —CH₂CH₂—) orethylidene (ethane-1,1-diyl, —CH(CH₃)—).

[0057] R¹ very particularly preferably represents hydrogen, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, represents in eachcase optionally fluorine- or chlorine-substituted propenyl, butenyl,propinyl or butinyl, represents in each case optionally fluorine-,chlorine- or methyl-substituted cyclopropyl or cyclopropylmethyl, orrepresents in each case optionally fluorine-, chlorine-, bromine-,methyl-, trifluoromethyl-, methoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl or benzyl.

[0058] R² very particularly preferably represents hydrogen, amino,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino,dimethylamino or diethylamino, represents in each case optionallyfluorine- or chlorine-substituted propenyl, butenyl, propinyl orbutinyl, represents in each case optionally fluorine-, chlorine- ormethyl-substituted cyclopropyl or cyclopropylmethyl, or represents ineach case optionally fluorine-, chlorine-, bromine-, methyl-,trifluoromethyl-, methoxy-, difluoromethoxy-, ortrifluoromethoxy-substituted phenyl, phenylamino or benzyl.

[0059] R³ very particularly preferably represents hydrogen, nitro,cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl ordiethylaminosulphonyl.

[0060] R⁴ very particularly preferably represents hydrogen, nitro,cyano, carbamoyl. thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl ordiethylaminosulphonyl.

[0061] m very particularly preferably represents the numbers 0, 1 or 2.

[0062] R⁵ very particularly preferably represents in each caseoptionally fluorine- or chlorine-substituted methyl, ethyl, n- ori-propyl, methylthio, ethylthio, n- or i-propylthio, or optionallyalso—if m represents 2—together with a second radical R⁵ representsethane-1,2-diyl (dimethylene).

[0063] R⁶ very particularly preferably represents hydroxyl.

[0064] R⁷ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, or represents optionally fluorine-, chlorine- ormethyl-substituted cyclopropyl.

[0065] R⁸ very particularly preferably represents hydrogen, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, represents in eachcase optionally fluorine- or chlorine-substituted propenyl, butenyl,propinyl or butinyl, represents in each case optionally fluorine-,chlorine- or methyl-substituted cyclopropyl or cyclopropylmethyl, orrepresents in each case optionally fluorine-, chlorine-, methyl-,trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl or benzyl.

[0066] R⁹ very particularly preferably represents hydroxyl, formyloxy,represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, acetyloxy,propionyloxy, methoxycarbonyloxy, ethoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, methylsulphonyloxy,ethylsulphonyloxy, represents in each case optionally fluorine- orchlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenylmethoxy,benzoyloxy, benzoylmethoxy or phenylsulphonyloxy.

[0067] R¹⁰ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, or represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, acetyl, propionyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, n- ori-propylthio.

[0068] R¹¹ very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or representsoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl.

[0069] R¹² very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or representsoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl.

[0070] R¹³ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, or represents in each case optionallyfluorine-, chlorine- or methoxy-substituted methyl, ethyl, n- ori-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl.

[0071] R³ most preferably represents (2)-chloro or (2)-trifluoromethyl.

[0072] R⁴ most preferably represents hydrogen, (4)-chloro or(4)-methylsulphonyl.

[0073] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred.

[0074] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0075] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0076] Very particular emphasis is given to the compounds of the generalformulae (I-1) to (I-6):

[0077] Here, n, A, R¹, R², R³, R⁴ and Z each have the meanings listedabove as being very particularly preferred.

[0078] Particular emphasis is given to the compounds of the formulae(I-1) to (I-6) in which Z represents Z¹ and Z¹ has the meaning listedabove as being very particularly preferred.

[0079] Particular emphasis is furthermore given to the compounds of theformulae (I-1) to (I-6) in which Z represents Z² and Z² has the meaninglisted above as being very particularly preferred.

[0080] Particular emphasis is furthermore given to the compounds of theformulae (I-1) to (I-6) in which Z represents Z³ and Z³ has the meaninglisted above as being very particularly preferred.

[0081] The following tautomeric forms of the compounds of the generalformula (I) are feasible:

[0082] In the case where Z=Z¹, if R⁶ represents hydroxyl:

[0083] In the case where Z=Z², if R⁹ represents hydroxyl:

[0084] In the case where Z=Z⁴:

[0085] Further tautomeric forms exist, depending on the substituents,and these also form part of the subject-matter of the invention.

[0086] The invention also preferably provides, if appropriate, sodium,potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium-,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts ofcompounds of the formula (I), in which n, A, R¹, R², R³, R⁴ and Z eachhave the leanings listed above as being preferred.

[0087] The abovementioned general or preferred radical definitions applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

[0088] The novel substituted aryl ketones of the general formula (I)have strong and selective herbicidal activity.

[0089] The novel substituted aryl ketones of the general formula (I)have strong and selective herbicidal activity.

[0090] The novel substituted aryl ketones of the general formula (I) areobtained when

[0091] (a) substituted benzoic acids of the general formula (II)

[0092] in which

[0093] n, A, R¹, R², R³ and R⁴ are each as defined above

[0094] —or reactive derivatives thereof, such as, for example, acidhalides, and cyanides or esters—

[0095] are reacted with compounds of the general formula (III)

Z—H  (III)

[0096] in which

[0097] Z is as defined above,

[0098] if appropriate in the presence of a dehydrating agent, ifappropriate in the presence of one or more reaction auxiliaries and ifappropriate in the presence of a diluent,

[0099] or when

[0100] (b) halogenoalkyl-aryl ketones of the general formula (IV)

[0101] in which

[0102] A, R³, R⁴ and Z are each as defined above and

[0103] X represents halogen

[0104] are reacted with compounds of the general formula (V)

[0105] in which

[0106] R¹ and R² are each as defined above and

[0107] M represents hydrogen or a metal equivalent,

[0108] if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

[0109] or when

[0110] (c) benzoyl ketones of the general formula (Ia)

[0111] in which

[0112] n, A, R¹, R², R³, R⁴ and R¹¹ are each as defined above,

[0113] are reacted with an orthoformic ester or anN,N-dimethyl-formamide acetal or with a cyanoformic ester or with carbondisulphide and an alkylating agent, and subsequently with hydroxylamineor an acid adduct thereof,

[0114] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,

[0115] and substitutions, oxidations or reductions within the scope ofthe definition of the substituents are carried out in a customarymanner, if appropriate subsequent to the processes (a), (b) or (c)according to the invention, on the resulting compounds of the generalformula (I), and/or the compounds of the general formula (I) areconverted in a customary manner into salt-like compounds.

[0116] Using, for example,4-chloro-3-[(1,4-dimethyl-5-oxo-4,5-dihydro-1H-2,4-triazol-3-yl)-sulphonyl]-2-fluoro-benzoicacid and 1,3-dimethyl-5-hydroxy-pyrazole as starting materials, thecourse of the reaction in the process (a) according to the invention canbe illustrated by the following equation:

[0117] Using, for example,2-(2-chloromethyl-4-trifluoromethyl-benzoyl)-1,3-cyclohexane-1,3-dioneand 4-ethyl-2-methyl-5-mercapto-2,4-dihydro-3H-1,2,4-triazo-3-one asstarting materials, the course of the reaction in the process (b)according to the invention can be illustrated by the following equation:

[0118] Using, for example,1-[2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-phenyl]-3-cyclopropyl-1,3-propanedione,ethyl cyanoformate and hydroxyl amine as starting materials, the courseof the reaction in the process (c) according to the invention can beillustrated by the following equation:

[0119] The formula (II) provides a general definition of the substitutedbenzoic acids to be used as starting materials in the process (a)according to the invention for preparing compounds of the generalformula (I). In the general formula (II), n, A, R¹, R², R³ and R⁴ eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for n, A, R¹, R², R³ and R⁴.

[0120] The starting materials of the general formula (II) are knownand/or can be prepared by processes known per se (cf. WO-A-96/35680).

[0121] The substituted benzoic acids of the general formula (II) areobtained when substituted benzoic acid derivatives of the generalformula (VI)

[0122] in which

[0123] n, A, R¹, R², R³ and R⁴ are each as defined above and

[0124] Y represents cyano or alkoxycarbonyl (in particularmethoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- ort-butoxycarbonyl)

[0125] are reacted with water, if appropriate in the presence of ahydrolysis auxiliary, such as, for example, hydrobromic acid, sulphuricacid or aqueous sodium hydroxide solution, and if appropriate in thepresence of an organic solvent, Such as, for example, dioxane, attemperatures between 50° C. and 120° C. (cf. the Preparation Examples).

[0126] The precursors of the general formula (VI) are known and/or canbe prepared by processes known per se (cf WO-A-96/35680, PreparationExamples).

[0127] The formula (III) provides a general definition of the compoundsfurther to be used as starting materials in the process (a) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (III), Z preferably has that meaning which has alreadybeen mentioned above, in connection with the description of thecompounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred or very particularly preferredfor Z.

[0128] The starting materials of the general formula (III) are knownand/or can be prepared by processes known per se.

[0129] The formula (IV) provides a general definition of thehalogenoalkyl-aryl ketones to be used as starting materials in theprocess (b) according to the invention for preparing compounds of thegeneral formula (I). In the general formula (IV), A, R³, R⁴ and Z eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for A, R³, R⁴ and Z; Xpreferably represents fluorine, chlorine, bromine or iodine, inparticular chlorine or bromine.

[0130] The starting materials of the general formula (IV) are knownand/or can be prepared by processes known per se (cf. EP-A-90 369,EP-A-93 488, EP-A-399 732, EP-A-480 641, EP-A-609 798, EP-A-763 524,DE-A-2 126 720, WO-A-93/03722, WO-A-97/38977, U.S. Pat. No. 3,978,127,U.S. Pat. No. 4,837,333).

[0131] The formula (V) provides a general definition of the compoundsfurther to be used as starting materials in the process (b) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (V), R¹ and R² each preferably have those meanings whichhave already been mentioned above, in connection with the description ofthe compounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred or very particularly preferredfor R¹ and R²; M preferably represents hydrogen or represents a lithium,sodium, potassium, rubidium, caesium, magnesium or calcium equivalent,in particular hydrogen, sodium or potassium.

[0132] The starting materials of the general formula (V) are knownand/or can be prepared by processes known per se (cf J. Med. Chem. 35(1992), 2573-2581; U.S. Pat. No. 3,767,666).

[0133] The formula (Ia) provides a general definition of the benzoylketones to be used as starting materials in the process (c) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (Ia), n, A, R¹, R², R³, R⁴ and R¹¹ each preferably havethose meanings which have already been mentioned above, in connectionwith the description of the compounds of the general formula (I)according to the invention, as being preferred, particularly preferredor very particularly preferred for n, A, R¹, R², R³, R⁴ and R¹¹.

[0134] The starting materials of the general formula (Ia) are novelcompounds according to the invention; they can be prepared by theprocess (a) or (b) according to the invention.

[0135] The process (a) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is preferablycarried out using a dehydrating agent. Suitable dehydrating agents arethe customary chemicals suitable for binding water.

[0136] Examples of these which may be mentioned aredicyclohexylcarbodiimide and carbonyldiimidazole.

[0137] A particularly suitable dehydrating agent which may be mentionedis dicyclohexylcarbodiimide.

[0138] The process (a) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is, ifappropriate, carried out using one or more reaction auxiliaries.

[0139] Examples of these which may be mentioned are sodium cyanide,potassium cyanide, acetone cyanohydrin,2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilylcyanide.

[0140] A particularly suitable further reaction auxiliary which may bementioned is trimethylsilyl cyanide.

[0141] The process (a) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is, ifappropriate, carried out using a further reaction auxiliary. Suitablefurther reaction auxiliaries for the process according to the inventionare, in general, basic organic nitrogen compounds, such as, for example,trimethylamine, triethylamine, tripropylamine, tributylamine,ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-di-cyclohexylamine, N,N-dimethyl-aniline,N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine,N-methyl-piperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

[0142] The process (c) according to the invention for preparing thecompounds of the formula (I) is, if appropriate, carried out usingorthoformic esters or N,N-dimethyl-formamide acetals. These compoundspreferably contain alkyl groups having 1 to 4 carbon atoms, inparticular methyl or ethyl. Examples which may be mentioned aretrimethyl orthoformate, triethyl orthoformate, N,N-dimethyl-form amidedimethyl acetal and N,N-dimethyl-formamide diethyl acetal.

[0143] The process (c) according to the invention for preparingcompounds of the formula (I) is, if appropriate, carried out usingcyanoformic esters. These compounds preferably contain alkyl groupshaving 1 to 4 carbon atoms, in particular methyl or ethyl. Exampleswhich may be mentioned are methyl cyanoformate and ethyl cyanoformate.

[0144] The process (c) according to the invention for preparingcompounds of the formula (I) is, if appropriate, carried out using(carbondisulphide and) alkylating agents. These compounds preferablycontain alkyl groups having 1 to 4 carbon atoms, in particular methyl orethyl. Examples which may be mentioned are methyl chloride, methylbromide, methyl iodide, dimethyl sulphate, ethyl chloride, ethylbromide, ethyl iodide and diethyl sulphate.

[0145] The process (c) according to the invention for preparingcompounds of the formula (I) is carried out using hydroxylamine or anacid adduct thereof. Hydroxylamine hydrochloride may be mentioned aspreferred acid adduct.

[0146] The processes (b) and (c) according to the invention forpreparing the compounds of the general formula (I) are preferablycarried out using a reaction auxiliary. Suitable reaction auxiliariesfor the processes (b) and (c) according to the invention are, ingeneral, the customary inorganic or organic bases or acid acceptors.These preferably include alkali metal or alkaline earth metal acetates,amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides,such as, for example, sodium acetate, potassium acetate or calciumacetate, lithium amide, sodium amide, potassium amide or calcium amide,sodium carbonate, potassium carbonate or calcium carbonate, sodiumbicarbonate, potassium bicarbonate or calcium bicarbonate, lithiumhydride, sodium hydride, potassium hydride or calcium hydride, lithiumhydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide,sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxideor potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- ort-butoxide; furthermore also basic organic nitrogen compounds, such as,for example, trimethylamine, triethylaamine, tripropylam ine,tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine,dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline,N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, 4-dimethyl-aminopyridine,N-methyl-piperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN) or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

[0147] The processes according to the invention for preparing thecompounds of the general formula (I) are preferably carried out usingdiluents. Suitable diluents for carrying out the processes (a), (b) and(c) according to the invention are especially inert organic solvents.These include, in particular, aliphatic, alicyclic or aromatic,optionally halogenated hydrocarbons, such as, for example, benzine,benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleumether, hexane, cyclohexane, dichloromethane, chloroform, carbontetrachloride; ethers, such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethyleneglycol diethyl ether; ketones, such as acetone, butanone or methylisobutyl ketone; nitrites, such as acetonitrile, propionitrile orbutyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether.

[0148] When carrying out the processes (a), (b) and (c) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably between 10° C. and 120° C.

[0149] The processes (a), (b) and (c) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to carry out the processes according to the invention underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

[0150] For carrying out the processes (a), (b) and (c) according to theinvention, the starting materials are generally employed inapproximately equimolar amounts. However, it is also possible to use arelatively large excess of one of the components. The reaction isgenerally carried out in a suitable diluent and the reaction mixture isgenerally stirred at the required temperature for several hours. Work-upis carried out by customary methods (cf. the Preparation Examples).

[0151] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

[0152] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0153] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaulea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0154] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0155] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Finibristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0156] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicium, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea. However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0157] The compounds are suitable, depending on the concentration, forthe total control of weeds, for example on industrial terrain and railtracks, and on paths and areas with and without tree plantings.Similarly, the compounds can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

[0158] The compounds of the formula (I) according to the invention aresuitable, in particular, for the selective control of monocotyledonousand dicotyledonous weeds in monocotyledonous crops, both by thepre-emergence and by the post-emergence method.

[0159] At certain concentrations or application rates, the activecompounds according to the invention can also be employed forcontrolling animal pests and fungal or bacterial plant diseases. Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

[0160] According to the invention, it is possible to treat all plantsand parts of plants. Plants are to be understood here as meaning allplants and plant populations such as desired and undesired wild plantsor crop plants (including naturally occurring crop plants). Crop plantscan be plants which can be obtained by conventional breeding andoptimization methods or by biotechnological and genetic engineeringmethods or combinations of these methods, including the transgenicplants and including plant cultivars which can or cannot be protected byplant breeders certificates. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of plants,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stems, trunks, flowers, fruit-bodies, fruits andseeds and also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

[0161] The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

[0162] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic substancesimpregnated with active compound, and microencapsulations in polymericsubstances.

[0163] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is to say liquidsolvents and/or solid carriers, optionally with the use of surfactants,that is to say emulsifiers and/or dispersants and/or foam-formers.

[0164] If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Liquid solvents whichare mainly suitable are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and water.

[0165] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

[0166] Tackifiers, Such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0167] It is possible to use colorants, such as inorganic pigments, forexample iron oxide, titanium oxide, Prussian blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients, such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0168] The formulations generally comprise between 0.1 and 95 percent byweight of active compound, preferably between 0.5 and 90%.

[0169] For controlling, weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides and/or substances which improve thecompatibility with crop plants (“safeners”), finished formulations ortank mixes being possible. Also possible are mixtures with weed-killerscomprising one or more known herbicides and a safener.

[0170] Possible components for the mixtures are known herbicides, forexample

[0171] acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amlidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazon, benzfendizone,benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox,bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor,butafenacil, butroxydim, butylate, cafenstrole, caloxydim, carbetamide,carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon,chlorimuron(-ethyl), chlomitrofen, chlorsulfuron, chlortoluron,cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimetihachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethamnetsulfuron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate,flucarbazone(-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl),flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorineochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl,-sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl),flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen,glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen,haloxyfop(-ethoxyethyl), haloxyfop)(-P-methyl), hexazinone,imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron,metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,pethoxamid, phenmedipham, picolinafen, piperophos, pretilachlor,primisulfuron(-methyl), procarbazone(-sodium), prometryn, propachlor,propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb,prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl),pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl),pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine,quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim,simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl),sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin and triflusulfuron, tritosulfuron.

[0172] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0173] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

[0174] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before

[0175] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0176] The preparation and the use of the active compounds according tothe invention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

[0177]

[0178] (Process (a))

[0179] A mixture of 0.80 g (2.5 mmol) of2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzoicacid, 0.28 g (2.5 mmol) of 1,3-cyclohexanedione and 0.63 g (3.1 mmol) ofN,N′-dicyclohexylcarbodiimide is stirred at room temperature(approximately 20° C.) for 48 hours. 0.7 ml (5 mmol) of triethylamineand a drop of trimethylsilyl cyanide are then added, and the mixture isstirred for a further 24 hours. The mixture is then concentrated underwater pump vacuum and the residue is stirred with 10% strength aqueoussodium carbonate solution. The mixture is then filtered and the filtrateis washed twice with diethyl ether, acidified with 2N hydrochloric acidand extracted with dichloromethane. The organic phase is dried overmagnesium sulphate and the solvent is removed under reduced pressure,giving 0.7 g (68% of theory) of2-[2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzoyl]-1,3-cyclohexanedioneas an oil (log P=2.00).

Example 2

[0180]

[0181] (Process (a))

[0182] A mixture of 1.45 g (5 mmol) of2-chloro-4-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoicacid, 0.70 g (6 mmol) of 1-ethyl-5-hydroxypyrazole, 1.3 g (6 mmol) ofdicyclohexylcarbodiimide and 100 ml of methylene chloride is stirred atroom temperature (approximately 20° C.) for 16 hours. The mixture isthen filtered and the filtrate is washed with water, dried with sodiumsulphate and filtered. The filtrated is concentrated and the residue istaken up in 50 ml of dioxane and heated under reflux with 1.4 g (10mmol) of potassium carbonate and 3 drops of trimethylsilyl cyanide for60 minutes. The mixture is then taken up in 150 ml of water and shakentwice with methylene chloride. 100 ml of methylene chloride are thenadded to the aqueous phase, and the mixture is acidified with stirringwith hydrochloric acid. The organic phase is separated off, dried withsodium sulphate and filtered. The filtrate is concentrated under waterpump vacuum, the residue is digested with diethyl ether and theresulting crystalline product is isolated by filtration with suction.

[0183] This gives 0.90 g (47% of theory) of5-[3-chloro-[4-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl]-carbonyl]-phenylsulphanyl]-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 216° C.

[0184] Analogously to Examples 1 and 2, and in accordance with thegeneral description of the preparation processes according to theinvention, it is also possible to prepare, for example, the compounds ofthe general formula (I) listed in Table 1 below. TABLE 1 (I)

Examples of compounds of the formula (I) Ex. (position) (position)(position) Physical No. n A R¹ R² R³ R⁴ Z data 3 0 (4) — CH₃ CH₃ (2) Cl—

4 0 (4) — H CH₃ (2) Cl —

m.p.: 98° C. 5 0 (4) — CH₃ CH₃ (2) Cl —

m.p.: 137° C. 6 0 (4) — CH₃ CH₃ (2) Cl —

logP =2.08 ^(a)) 7 2 (4) — H CH₃ (2) Cl —

m.p.: 213° C. 8 0 (4) — CH₃ CH₃ (2) Cl —

m.p.: 140° C. 9 0 (4) — CH₃ CH₃ (2) Cl —

logP =1.34 ^(a)) 10 2 (4) — CH₃ CH₃ (2) Cl —

m.p.: 164° C. 11 2 (4) — CH₃ CH₃ (2) Cl —

m.p.: 187° C. 12 2 (4) — CH₃ CH₃ (2) Cl —

m.p.: 225° C. 13 2 (4) — CH₃ CH₃ (2) Cl —

logP =2.09 ^(a)) 14 2 (4) — H CH₃ (2) Cl —

logP =1.88 ^(a)) 15 0 (2) — CH₃ CH₃ (4) CF₃ —

16 0 (2) CH₂ CH₃ CH₃ (4) CF₃ —

logP =2.41 ^(a)) 17 0 (2) CH₂ CH₃ CH₃ (4) CF₃ —

logP =2.16 ^(a)) 18 0 (3) CH₂ H CH₃ (2) Cl (4) Cl

m.p.: 187° C. 19 0 (3) CH₂ H CH₃ (2) Cl (4) Cl

logP =1.61 ^(a)) 20 0 (3) CH₂ CH₃ CH₃ (2) Cl (4) Cl

logP =2.24 ^(a)) 21 0 (3) CH₂ CH₃ CH₃ (2) Cl (4) Cl

logP =1.82 ^(a)) 22 1 (3) CH₂ H CH₃ (2) Cl (4) Cl

logP =1.60 ^(a)) 23 2 (3) CH₂ CH₃ CH₃ (2) Cl (4) Cl

logP =2.09 ^(a)) 24 2 (3) CH₂ CH₃ CH₃ (2) Cl (4) Cl

logP =1.62 ^(a)) 25 2 (3) CH₂ H CH₃ (2) Cl (4) Cl

logP =1.87 ^(a)) 26 2 (3) CH₂ H CH₃ (2) Cl (4) Cl

logP =1.45 ^(a)) 27 1 (3) CH₂ CH₃ CH₃ (2) Cl (4) Cl

logP =1.42 ^(a)) 28 1 (3) CH₂ H CH₃ (2) Cl (4) Cl

logP =1.61 ^(a)) 29 0 (3) CH₂ H CH₃ (2) Cl (4) SO₂CH₃

30 1 (3) CH₂ H CH₃ (2) Cl (4) SO₂CH₃

31 2 (3) CH₂ H CH₃ (2) Cl (4) SO₂CH₃

32 0 (3) CH₂ CH₃ CH₃ (2) Cl (4) SO₂CH₃

33 1 (3) CH₂ CH₃ CH₃ (2) Cl (4) SO₂CH₃

34 2 (3) CH₂ CH₃ CH₃ (2) Cl (4) SO₂CH₃

35 0 (3) CH₂ C₂H₅ CH₃ (2) Cl (4) SO₂CH₃

36 1 (3) CH₂ C₂H₅ CH₃ (2) Cl (4) SO₂CH₃

37 2 (3) CH₂ C₂H₅ CH₃ (2) Cl (4) SO₂CH₃

38 0 (3) CH₂ H CH₃ (2) Cl (4) SO₂CH₃

39 1 (3) CH₂ H CH₃ (2) Cl (4) SO₂CH₃

40 2 (3) CH₂ H CH₃ (2) Cl (4) SO₂CH₃

41 0 (3) CH₂ CH₃ CH₃ (2) Cl (4) SO₂CH₃

42 1 (3) CH₂ CH₃ CH₃ (2) Cl (4) SO₂CH₃

43 2 (3) CH₂ CH₃ CH₃ (2) Cl (4) SO₂CH₃

44 0 (3) CH₂ C₂H₅ CH₃ (2) Cl (4) SO₂CH₃

45 1 (3) CH₂ C₂H₅ CH₃ (2) Cl (4) SO₂CH₃

46 2 (3) CH₂ C₂H₅ CH₃ (2) Cl (4) SO₂CH₃

47 0 (4) — C₂H₅ CH₃ (2) Cl —

logP =2.34 ^(a)) 48 0 (4) — C₂H₅ CH₃ (2) Cl —

m,p,: 150° C. 49 0 (4) — n-C₃H₇ CH₃ (2) Cl —

logP =2.63 ^(a)) 50 0 (4) — n-C₃H₇ CH₃ (2) Cl —

logP =2.14 ^(a)) 51 0 (4) —

CH₃ (2) Cl —

logP =2.47 ^(a)) 52 0 (4) —

CH₃ (2) Cl —

logP =2.00 ^(a)) 53 0 (4) —

CH₃ (2) Cl —

logP =2.37 ^(a)) 54 0 (4) —

CH₃ (2) Cl —

logP =1.90 ^(a)) 55 0 (4) —

CH₃ (2) Cl —

logP =2.72 ^(a)) 56 0 (4) —

CH₃ (2) Cl —

logP =2.22 ^(a)) 57 0 (4) —

CH₃ (2) Cl —

logP =3.04 ^(a)) 58 0 (4) —

CH₃ (2) Cl —

logP =2.55 ^(a)) 59 0 (4) — H

(2) Cl —

60 0 (4) — H

(2) Cl —

61 0 (4) — H OC₂H₅ (2) Cl —

62 0 (4) — H OC₂H₅ (2) Cl —

63 0 (4) — CH₃

(2) Cl —

64 0 (4) — CH₃

(2) Cl —

65 0 (4) — CH₃ OC₂H₅ (2) Cl —

66 0 (4) — CH₃ OC₂H₅ (2) Cl —

67 0 (4) — CH₃ CH₃ (2) Cl —

68 2 (2) — CH₃ CH₃ (4) CF₃ —

logP =1.85 ^(a)) 69 2 (2) — CH₃ CH₃ (4) CF₃ —

logP =1.72 ^(a)) 70 1 (2) CH₂ CH₃ CH₃ (4) CF₃ —

logP =1.95 ^(a)) 71 1 (2) CH₂ CH₃ CH₃ (4) CF₃ —

logP =1.77 ^(a))

[0185] Calibration was carried out using unbranched alkan-2-ones (with 3to 16 carbon atoms) whose logP values are known (determination of thelogP values by the retention times using linear interpolation betweentwo successive alkanones).

[0186] The lambda-max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

[0187] The compound listed above in Table 1 as Example 3 can beprepared, for example, as follows:

[0188] (Process (c))

[0189] A mixture of 5.0 g (13.7 mmol) of1-[2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-phenyl]-3-cyclopropyl-1,3-propanedione(cf. Example 67), 1.5 g (17 mmol) of N,N-dimethyl-formamide dimethylacetal and 50 ml of toluene is stirred at 90° C. for 18 hours and thenconcentrated under water pump vacuum. The residue is taken up in 50 mlof ethanol and admixed with 0.95 g (13.7 mmol) of hydroxylaminehydrochloride. The reaction mixture is then stirred at room temperature(approximately 20° C.) for 2 hours and subsequently concentrated underwater pump vacuum. The residue is shaken with water/methylene chlorideand the organic phase is washed with saturated aqueous sodium chloridesolution, dried with sodium sulphate and filtered. The filtrate isconcentrated under water pump vacuum and the residue is purified bycolumn chromatography (silica gel, cyclohexane/ethyl acetate, vol.:7:3):

[0190] This gives 0.13 g (2.5% of theory) of5-[3-chloro-4-[(5-cyclopropyl-isoxazol-4-yl)-carbonyl]-phenylsulphanyl]-2,4-dihydro-2,4-dimethyl-3H-1,2,4-triazol-3-one.

[0191] The compound listed above in Table 1 as Example 22 can beprepared, for example, as follows:

[0192] (Subsequent Reaction)

[0193] 1.4 g (3 mmol) of2-[2,4-dichloro-3-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanylmethyl]-benzoyl]-1,3-cyclohexanedione(cf. Example 18) are initially charged in 100 ml of methylene chlorideand admixed with 0.35 g (7.5 mmol) of formic acid, 1.1 g of aqueoushydrogen peroxide (30% strength, i.e. 9 mmol of H₂O₂) and a spatula tipof ammonium molybdate. The reaction mixture is stirred at roomtemperature (approximately 20° C.) for 24 hours, subsequently washedwith water, then with 1 N aqueous sodium hydroxide solution and againwith water and finally with saturated aqueous sodium chloride solution,dried with sodium sulphate and filtered. From the filtrate, the solventis carefully distilled off under reduced pressure.

[0194] This gives 1.0 g (75% of theory) of2-[2,4-dichloro-3-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphinylmethyl]-benzoyl]-1,3-cyclohexanedione.

[0195] The compound listed above in Table 1 as Example 67 can beprepared, for example, as follows:

[0196] (Process (a))

[0197] 3.7 g (44 mmol) of cyclopropyl methyl ketone are initiallycharged in 80 ml of acetone and admixed with 1.32 g of sodium hydride(75% pure, 44 mmol of NaH). The mixture is stirred at room temperature(approximately 20° C.) for 30 minutes and then admixed with a suspensionof 8.0 g (22 mmol) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoate—cf.Example (II 4)— and 1 g of dibenzo-18-crown-6 in 40 ml of acetone. Thereaction mixture is heated under reflux for 60 minutes and, aftercooling to room temperature, admixed with approximately the same amountby volume of saturated aqueous ammonium chloride solution and thenshaken with ethyl acetate. The organic phase is dried with sodiumsulphate and filtered. From the filtrate, the solvent is carefullydistilled off under reduced pressure.

[0198] This gives 6.0 g (75% of theory) of1-[2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-phenyl]-3-cyclopropyl-1,3-propanedione.

[0199] Starting Materials of the Formula (II):

Example (II-1)

[0200]

[0201] A mixture of 2.0 g (6.7 mmol) of2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzonitrileand 25 ml of 48% strength aqueous hydrobromic acid is heated at 40° C.for 5 hours. The yellow suspension is diluted with 10 ml of water andfiltered. At 50° C., the residue is stirred with 40 ml of saturatedaqueous sodium bicarbonate solution, and undissolved solid is filteredoff. The filtrate is acidified with 2 N hydrochloric acid and theresulting precipitate is filtered off and dried under reduced pressure.

[0202] This gives 1.0 g (47% of theory) of2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzoicacid of melting point 229° C.

Example (II-2)

[0203]

[0204] A mixture of 3.0 g (9.5 mmol) of2-[(1,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzonitrileand 30 ml of 48% strength aqueous hydrobromic acid is heated at 95° C.for 12 hours. The suspension is diluted with 20 ml of water andfiltered. At 50° C., the residue is stirred with 40 ml of saturatedaqueous sodium bicarbonate solution and undissolved solid is filteredoff. The filtrate is acidified with 2N hydrochloric acid and theresulting precipitate is filtered off and dried under reduced pressure.

[0205] This gives 1.85 g (58% of theory) of2-[(1,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzoicacid of melting point 211° C.

Example (II-3)

[0206]

[0207] 5.4 g (15 mmol) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoateare, in a mixture of 50 ml of dioxane, 50 ml of water and 1.2 g (30mmol) of sodium hydroxide, heated at 80° C. for 60 minutes. The mixtureis then diluted with 100 ml of water, acidified to pH=2 using conc.hydrochloric acid and then admixed with methylene chloride. Theresulting crystalline product is isolated by filtration with suction.

[0208] This gives 2.9 g (67% of theory) of2-chloro-4-[(4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoicacid of melting point 236° C.

Example (II-4)

[0209]

[0210] 7.4 g (20 mmol) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoicacid are, in a mixture of dioxane, 50 ml of water and 1 g (25 mmol) ofsodium hydroxide, heated with stirring at 80° C. for 60 minutes. Themixture is then concentrated under water pump vacuum to about half itsoriginal volume, diluted with 100 ml of water and acidified with 10%strength hydrochloric acid. The resulting crystalline product isisolated by filtration with suction.

[0211] This gives 4.9 g (81% of theory) of2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoicacid of melting point 222° C.

[0212] Analogously to Examples (II-1) to (II-4), it is also possible toprepare, for example, the compounds of the general formula (II) listedin Table 2 below.

TABLE 2 Examples of compounds of the formula (II) Ex. (position)(position) (position) No. n A R¹ R² R³ R⁴ Physical data II-5 2 (4) H CH₃(2) — m.p.: 285° C. — Cl II-6 2 (4) CH₃ CH₃ (2) — m.p.: 298° C. — ClII-7 0 (3) H CH₃ (2) (4) m.p.: 227° C. CH₂ Cl Cl II-8 0 (3) CH₃ CH₃ (2)(4) m.p.: 203° C. CH₂ Cl Cl II-9 0 (2) CH₃ CH₃ (4) — logP = 1.94 ^(a))CH₂ CF₃ II-10 0 (4) C₂H₅ CH₃ (2) — m.p.: 168° C. — Cl II-11 0 (4) n-C₃H₇CH₃ (2) — m.p.: 172° C. — Cl II-12 0 (4) —

CH₃ (2) Cl — m.p.: 160° C. II-13 0 (4) —

CH₃ (2) Cl — m.p.: 153° C. II-14 0 (4) —

CH₃ (2) Cl — m.p.: 172° C. II-15 0 (4) —

CH₃ (2) Cl — m.p.: 177° C.

[0213] The compound listed above in Table 2 as Example (II-9) can, forexample, be prepared as follows:

[0214] 11.5 g (31.9 mmol) of methyl2-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanylmethyl]-4-trifluoromethyl-benzoateare initially charged in 200 ml of cyclohexane and admixed with 50 ml of2-methoxy-ethanol and then with 1.8 g of potassium hydroxide. Thereaction mixture is stirred at room temperature (approximately 20° C.)for 2 hours and then poured into 200 ml of water. After shaking with 2Nhydrochloric acid, the resulting crystalline product is isolated byfiltration with suction.

[0215] This gives 7.5 g (68% of theory) of2-[(4,5-dihydro-1,4-dimethyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanylmethyl]-4-trifluoromethyl-benzoicacid.

[0216] Intermediates of the Formula (VI):

Example (VI-1)

[0217]

[0218] 48.4 g (0.20 mol) of neopentyl 4-amino-2-chloro-benzoate (cf.DE-A-2 445 529) are taken up in 100 ml of water and, with stirring,admixed dropwise with 100 g of conc. hydrochloric acid. At −5° C., asolution of 14.1 g (0.20 mol) of sodium nitrite in 40 ml of water isadded dropwise with stirring to the above mixture. The resultingsolution is then quickly added dropwise with vigorous stirring to amixture of 26.2 g (0.20 mol) of5-mercapto-4-methyl-2,4-dihydro-1,2,4-triazol-3-one, 8.0 g (0.20 mol) ofsodium hydroxide, 40.8 g (0.3 mol) of sodium acetate trihydrate, 2 g ofcopper(II) chloride dihydrate, 300 ml of water and 300 ml of methylenechloride, a temperature increase to about 30° C. and evolution of gasbeing observed. After 30 minutes of stirring, the organic phase isseparated off, washed with water, dried with sodium sulphate andfiltered. The filtrate is concentrated under water pump vacuum and theresidue is recrystallized from diisopropyl ether.

[0219] This gives 26.7 g (37% of theory) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoateof melting point 138° C. Example (VI-2)

[0220] 21.4 g (60 mmol) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoateare taken up in 150 ml of acetone and, with 13.8 g (0.1 mol) ofpotassium carbonate and 14.2 g (0.1 mol) of iodomethane, heated underreflux for 16 hours. The mixture is then concentrated under water pumpvacuum and the residue is taken up in methylene chloride and acidifiedslightly using 1N hydrochloric acid. The organic phase is once againwashed with water and with saturated aqueous sodium chloride solution,dried with sodium sulphate and filtered. The filtrate is concentratedunder water pump vacuum, the residue is digested with petroleum etherand the resulting crystalline product is isolated by filtration withsuction.

[0221] This gives 20.5 g (92% of theory) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-1,4-dimethyl-5-oxo-H-1,2,4-triazol-3-yl)-sulphanyl]-benzoateof melting point 101° C.

Example (VI-3)

[0222]

[0223] 3.6 g (10 mmol) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphanyl]-benzoateare taken up in 150 ml of methylene chloride and admixed with 10 g of3-chloro-perbenzoic acid. After 16 hours of stirring at 20° C., themixture is washed with aqueous sodium hydrogen sulphite solution, thenwith water and finally with saturated aqueous sodium chloride solution.The organic phase is concentrated under water pump vacuum, the residueis digested with diethyl ether and the resulting crystalline product isisolated by filtration with suction.

[0224] This gives 3.3 g (85% of theory) of 2,2-dimethyl-propyl2-chloro-4-[(4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)-sulphonyl]-benzoateof melting point 177° C.

Example (VI-4)

[0225]

[0226] Over a period of 2 hours, 14 g (65 mmol) of2-nitro-4-trifluoromethyl-benzonitrile are added to a mixture of 10 g(76 mmol) of 4-methyl-5-sulphanyl-2,4-dihydro-3H-1,2,4-triazol-3-one and22.5 g (163 mmol) of potassium carbonate in 100 ml of dimethylsulphoxide. After 4 hours of stirring at 50° C., most of the solvent isremoved under reduced pressure and the residue is introduced into water.The precipitated solid is filtered off, dried and recrystallized fromn-propanol.

[0227] This gives 6.5 g (33% of theory) of2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3yl)-sulphanyl]-4-trifluoromethyl-benzonitrileof melting point 182° C. (with decomp.).

Example (VI-5)

[0228]

[0229] 2.5 g (17.6 mmol) of iodomethane are added to a mixture of 5.0 g(16.7 mmol) of2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzonitrileand 4.6 g (33.4 mmol) of potassium carbonate in 50 ml of acetonitrile,and the reaction mixture is heated at 50° C. for 6 hours. The solvent isthen removed under reduced pressure and the oily residue is taken up inwater and dichloromethane. The organic phase is separated off and driedover magnesium sulphate, and the solvent is removed under reducedpressure.

[0230] This gives 5.1 g (97% of theory) of2-[(1,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzonitrileof melting point 113° C.

[0231] Analogously to Examples (VI-1) to (VI-5), it is also possible toprepare, for example, the compounds of the general formula (VI) listedin Table 3 below.

TABLE 3 Examples of compounds of the formula (VI) Ex. (position)(position) (position) Physical No. n A R¹ R² R³ R⁴ Y data VI-6 2 (4) —CH₃ CH₃ (2) Cl —

m.p.: 114° C. VI-7 0 (3) CH₂ H CH₃ (2) Cl (4) Cl

m.p.: 111° C. VI-8 0 (3) CH₂ CH₃ CH₃ (2) Cl (4) Cl

logP =2.12 ^(a)) VI-9 0 (4) — C₂H₅ CH₃ (2) Cl —

logP =3.80 ^(a)) VI-10 0 (4) — n-C₃H₇ CH₃ (2) Cl —

logP =4.19 ^(a)) VI-11 0 (4) —

CH₃ (2) Cl —

logP =3.92 ^(a)) VI-12 0 (4) —

CH₃ (2) Cl —

logP =3.70 ^(a)) VI-13 0 (4) —

CH₃ (2) Cl —

logP =4.27 ^(a)) VI-14 0 (4) —

CH₃ (2) Cl —

logP =4.51 ^(a)) VI-15 0 (2) — CH₃ CH₃ (4) CF₃ — CN m.p.: 113° C. VI-16(2) CH₂ CH₃ CH₃ (4) CF₃ —

logP =2.48 ^(a))

[0232] USE EXAMPLES:

Example A

[0233] Pre-Emergence Test

[0234] Solvent: 5 parts by weight of acetone

[0235] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0236] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0237] Seeds of the test plants are sown in normal soil. After 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of active compound in the spray liquor is chosenso that the particular amount of active compound desired is applied in1000 litres of water per hectare.

[0238] After three weeks, the degree of damage to the plants is rated in% damage ill comparison to the development of the untreated control. Thefigures denote:

[0239] 0%=no effect (like untreated control)

[0240] 100%=total destruction

[0241] In this test, for example, the compounds of Preparation Examples1 and 15 exhibit strong activity against weeds, and they are toleratedwell by some crop plants, Such as, for example, cotton, maize, soya andwheat.

Example B

[0242] Post-Emergence Test

[0243] Solvent: 5 parts by weight of acetone

[0244] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0245] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0246] Test plants of a height of 5 to 15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen so that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

[0247] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0248] The figures denote:

[0249] 0%=no effect (like untreated control)

[0250] 100%=total destruction

[0251] In this test, for example, the compounds of Preparation Examples1 and 15 exhibit strong activity against weeds, and they are toleratedwell by crop plants, such as, for example, maize.

1. Substituted aryl ketones of the general formula (I)

in which n represents the numbers 0, 1 or 2, A represents a single bondor represents alkanediyl, R¹ represents hydrogen or represents in eachcase optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aryl or arylalkyl, R² represents hydrogen, amino, orrepresents in each case, optionally substituted alkyl, alkoxy,alkylamino, dialkylamino, alkenyl, alkenyloxy, alkinyl, alkinyloxy,cycloalkyl, cycloalkylalkyl, aryl, arylamino or arylalkyl, R³ representshydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphonyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl, R⁴ representshydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphony), and Z represents oneof the groupings below

where m represents the numbers 0 to
 6. R⁵ represents halogen orrepresents in each case optionally substituted alkyl or alkylthio, or—ifm represents 2-together with a second radical R⁵ represents alkanediyl(alkylene), R⁶ represents hydroxyl, formyloxy, or represents in eachcase optionally substituted alkoxy, alkylthio, alkoxycarbonyloxy,alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy,alkinyloxy, arylalkyl, aryloxy, arylthio, arylcarbonyloxy,arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy or arylalkylthio, R⁷represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl or cycloalkyl, R⁸represents hydrogen or represents in each case optionally substitutedalkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,R⁹ represents hydroxyl, formyloxy, or represents in each case optionallysubstituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkyloxy,arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy, R¹⁰represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl or alkylthio, R¹¹ represents hydrogen orrepresents in each case optionally substituted alkyl or cycloalkyl, R¹²represents hydrogen or represents in each case optionally substitutedalkyl or cycloalkyl, and R¹³ represents hydrogen, cyano, carbamoyl,halogen, or represents in each case optionally substituted alkyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,including all possible tautomeric forms of the compounds of the generalformula (I) and the possible salts of the compounds of the generalformula (I).
 2. Compounds according to claim 1, characterized in that Arepresents a single bond or represents alkanediyl having 1 to 6 carbonatoms, R¹ represents hydrogen, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents ineach case optionally cyano- or halogen-substituted alkenyl or alkinylhaving in each case 2 to 6 carbon atoms, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6or carbon atoms in the aryl group and optionally 1 to 4 carbon atoms inthe alkyl moiety, R² represents hydrogen, amino, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy,alkylamino or di-alkylamino having in each case 1 to 6 carbon atoms inthe alkyl groups, represents in each case optionally cyano- orhalogen-substituted alkenyl, alkenyloxy, alkinyl or alkinyloxy having ineach case 2 to 6 carbon atoms, represents in each case optionallycyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl, arylamino or arylalkyl having ineach case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4carbon atoms in the alkyl moiety, R³ represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl havingin each case 1 to 6 carbon atoms in the alkyl groups, and R⁴ representshydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl halogen, orrepresents in each case: optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups.
 3. Compounds according to claim 1 or 2, characterized inthat m represents the numbers 0, 1, 2, 3 or 4, R⁵ represents halogen orrepresents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl or alkylthio having in each case, 1 to 6carbon atoms, or optionally also—if m represents 2—together with asecond radical R⁵ represents alkanediyl (alkylene) having 2 to 6 carbonatoms, R⁶ represents hydroxyl, formyloxy, or represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkoxy,alkylthio, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy oralkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkylgroups, represents in each case optionally cyano- or halogen-substitutedalkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, orrepresents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted arylalkyl, aryloxy, arylthio,arylcarbonyloxy arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy orarylalkylthio having in each case 6 or 10 carbon atoms in the aryl groupand optionally 1 to 4 carbon atoms in the alkyl moiety. R⁷ representshydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonylhaving in each case 1 to 6 carbon atoms in the alkyl groups, orrepresents optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl having 3 to 6 carbon atoms, R⁸ represents hydrogen,represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents ineach case optionally cyano- or hydrogen-substituted alkenyl or alkinylhaving in each case 2 to 6 carbon atoms, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atomsin the alkyl moiety, R⁹ represents hydroxyl, formyloxy, represents ineach case optionally cyano-, halogen- or C₁-C₄-alkoxy-substitutedalkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy oralkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkylgroups, represents in each case optionally cyano- or halogen-substitutedalkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, orrepresents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₁-halogenoalkoxy-substituted arylalkoxy, arylcarbonyloxy,arylcarbonylalkoxy or alkylsulphonyloxy having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety, R¹⁰ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl oralkylthio having in each case; 1 to 6 carbon atoms in the alkyl groups,R¹¹ represents hydrogen, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms or representsoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having3 to 6 carbon atoms, R¹² represents hydrogen, represents optionallycyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbonatoms or represents optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, and R¹³represents hydrogen, cyano, carbamoyl, halogen, or represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonylhaving in each case 1 to 6 carbon atoms in the alkyl groups. 4.Compounds according to claim 1, characterized in that A represents asingle bond or represents alkanediyl having 1 to 4 carbon atoms, R¹represents hydrogen, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, represents in each case optionallycyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl,propinyl or butinyl, represents in each case optionally cyano-,fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- ort-butoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,benzyl or phenylethyl, R² represents hydrogen, amino, represents in eachcase optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,ethylamino, n- or i-propylamino, n-, i- or s-butylamino, dimethylaminoor diethylamino, represents in each case optionally cyano-, fluorine-,chlorine- or bromine-substituted propenyl, butenyl, propenyloxy,butenyloxy, propinyl, butinyl, propinyloxy or butinyloxy, represents ineach case; optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylamino, benzyl or phenylethyl,R³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl,n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,dimethylamino, diethylamino, dimethylaminosulphonyl ordiethylaminosulphonyl, and R⁴ represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-,s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-,s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonylor diethylaminosulphonyl.
 5. Compounds according to any of claim 1 to 4,characterized in that m represents the numbers 0, 1, 2 or 3, R⁵represents fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, or optionallyalso—if m represents 2-together with a second radical R⁵ representsethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) orbutane-1,4-diyl (tetramethylene), R⁶ represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-,s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy,prophyloxy or butonyloxy, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenoxy, phenylthio, benzoyloxy,benzoylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio orbenzyl, R⁷ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,fluorine, chlorine, bromine, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio,:n-,i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, or represents in each case optionally cyano-,fluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R⁸ representshydrogen, represents in each case optionally cyano-, fluorine-,chlorine-, bromine-, methoxy- or ethoxy-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, represents in each case optionallycyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl,propinyl or butinyl, represents in each case optionally cyano-,fluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- ort-butoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl orbenzyl, R⁹ represents hydroxyl, formyloxy, represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy,prophyloxy or butinyloxy, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenylmethoxy, benzoyloxy, benzoylmethoxyor phenylsulphonyloxy, R¹⁰ represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, n-, I-, or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- , ori-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-or t-butylthio, R¹¹ represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cylobutyl,cyclopentyl or cyclohexyl, R¹² represents hydrogen, represents in eachcase optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, and R¹³ represents hydrogen, cyano,carbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, or t-butoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxy-carbonyl, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl.
 6. Process for preparingcompounds according to any of claims 1 to 5, characterized in that (a)substituted benzoic acids of the general formula (II)

in which n, A, R¹, R², R³ and R⁴ are each as defined in any of claims 1,2 and 4, or reactive derivatives thereby; are reacted with compounds ofthe general formula (III) Z—H  (III) in which Z is as defined in any ofclaims 1, 3 and 5, if appropriate in the presence of a dehydratingagent, if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of a diluent, or that (b)halogenoalkyl-aryl ketones of the general formula (IV)

in which A, R³, R⁴ and Z are each as defined in any of claims 1 to 5 andX represents halogen are reacted with compounds of the general formula(V)

in which R¹ and R² are defined in any of claims 1, 2 and 4 and Mrepresents hydrogen or a metal equivalent, if appropriate in thepresence of a reaction auxiliary and if appropriate in the presence of adiluent, or that (c) benzoyl ketone of the general formula (Ia)

in which n, A, R¹, R³, R⁴ and R¹¹ are each as defined any of claims 1 to5, are reacted with an orthoformic ester or an N,N-dimethyl-formamideacetal or with a cyanoformic ester or with carbon disulphide and analkylating agent, and subsequently with hydroxylamine or an acid adductthereof, if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,and substitutions, oxidations or reductions within the scope of thedefinition of the substituents are carried out in a customary manner, ifappropriate subsequent to the processes (a), (b) or (c) according to theinvention, on the resulting compounds of the general formula (I), and/orthe compounds of the general formula (I) are converted in a customarymanner into salt-like compounds.
 7. Benzoyl ketones of the generalformula (Ia)

in which n, A, R¹, R², R³, R⁴ and R¹¹ are each as defined in any ofclaims 1 to
 5. 8. Use of at least one compound according to any ofclaims 1 to 5 for controlling undesirable plants.
 9. Compositions,characterized in that they comprise at least one compound according toany of claims 1 to 5 and customary extenders.